Chicago

Chicago is my favorite city in the United States. I’ve had a crush on the place for several years now. If this is your first time to the city, you should consider yourself one lucky business traveler! That is, unless you’re visiting between the months of November and around March when it’s too frosty to properly enjoy the place.

Getting There & Around

Chicago is serviced by the two major airports of Midway and O’Hare. You can get a rental car, take a cab or catch the “L” (the elevated train) directly from both airports. O’Hare is a hub for United Airlines and American Airlines and Midway serves as a Southwest hub, so you should have no trouble reaching the city wherever you are in the world.

AmTrak and bus services like MegaBus offer frequent travel to and from Chicago from various cities throughout the Midwest and beyond.

The L is the subway system for the city. It isn’t nearly as comprehensive as the New York subway system, but it definitely gets you where you need to go. You just may need to catch a bus to get you the rest of the way there.

Business Hotels

Embassy Suites Lakefront (home to one of the best hotel fitness centers in America)
Omni Chicago Hotel (offer Cathedral District tours)

Entertainment

Chicago is a big city on a manageable level. Sports fans will enjoy themselves with Wrigley Field and Comiski Park. In the winter, you can watch the Chicago Bulls or a variety of other sports. Broadway in Chicago offers spectacular productions throughout the season. I was lucky enough to see Wicked at the Oriental Theater, and it was an amazing production. Hiking and jogging are available on the lake shore, with guided running tours available. Shoppers will keep busy on the Magnificent Mile. On certain days, L Tours are available showcasing the history of the city. And, of course no trip to the city is complete without a visit to the Art Institute of Chicago.